


Accidental Skirt Shopping

by BabyBat (BabyBatsCreations)



Category: Supernatural
Genre: Crossdressing, Hand Jobs, Kissing, M/M, Requited Love, Semi-Public Sex, Underage - Freeform
Language: English
Status: Completed
Published: 2018-08-06
Updated: 2018-08-06
Packaged: 2019-06-22 21:40:10
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,848
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15591282
Author URL: https://archiveofourown.org/users/BabyBatsCreations/pseuds/BabyBat
Summary: Dean and Sam split up while out shopping. Dean catches Sam trying on a skirt in the dressing room.





	Accidental Skirt Shopping

“Alright, here's the list. You go and get some food. I'm going to see if I can find all of this in the hardware section. We'll meet up front by the fifth register. Got it?”

Sam sighed petulantly at his older brother. “Yeah, Dean I got it.” He started marching off to the left side of the store before Dean could boss him around some more.

“And no name brand stuff!” Dean shouted after him before heading off in the opposite direction.

A comment like that might have embarrassed Sam any other time, but it was well after midnight, technically after curfew for a small town like this, and the place was mostly empty. There was only a single register open, lane 5, the cigarette lane of course. The only other worker seemed to be a man pushing around a large broom and talking to himself. It was a little bit creepy how abandoned the place was.

Sam marched up and down the grocery aisles, his adolescent feet slapping on the linoleum floor. He threw everything from off-brand “toaster pastries” to off-brand “spaghetti-rounds” into his hand basket. If he happened to slip a few small things into the inner pocket of his jacket, well there was no one around to accuse him now was there?

He made his way back towards the front only to be distracted by the brilliantly colored array of girl's skirts. Sam looked around, stood up on his toes to look over the racks, and then checked over his shoulder before picking one up.

The skirt was short and a color somewhere between royal blue and cerulean that spoke of cheap dye. It was made for a much younger girl than Sam was, but his hips were narrow enough that when he held it against his body, it looked like it might fit. Sam bit his lip and looked around one more time in case he was being watched. He didn't see anyone around, but he did see a women's dressing room just a few feet away. There was no one on duty watching the stalls which were covered enough that no one would be able to see Sam at all once he was inside.

Sam walked over to the dressing rooms and reached for the handle on the first one. Part of him hoped it would be locked, but another part of him was pleased when it wasn't. He went in and he closed the door behind him.

The room was empty besides a small bench and two hooks on the walls where a few empty hangers hung. Sam set his coat and the basket on the bench. He faced the mirror and hesitantly lifted the skirt up to his waist again. The color was pretty and the skirt was a style that he'd always liked on the girls he'd seen at school, though it was definitely too short for any of them to get away with wearing. Not that it mattered to Sam who would definitely not be wearing this skirt to school or at all in fact. What was he even doing in here? He wasn't really going to try on a freaking skirt was he? He shivered at the thought... Yes. Yes, he was.

He set the skirt down to take off his pants. Pulling the skirt off the hanger, he almost lost his nerve, but he stepped into it anyway and slid it up to his hips. It fit snug, but comfortable around his waist. Still, he was scared to turn around and look at himself in the mirror.

It didn't make sense to go to all the trouble of sneaking in here and putting it on just to chicken out. So, Sam took a deep breath, closed his eyes, and turned around. When he opened his eyes, Sam moaned and his knees went weak.

The skirt was a good six inches above his knees. It was pretty and feminine and it made Sam look pretty and feminine so much so that he started to blush. He knew he was hard under that skirt, but he couldn't be bothered to feel the least bit ashamed because he looked so damn sexy. He couldn't help but close his eyes imagining someone bigger and stronger than him, bending him over right there and fucking him in his little skirt. He whimpered and his hands reached out to catch himself on the wall before he could out right collapse.

Then the door clicked. Sam gasped and whirled around to see his brother, slowly pulling the door open. He grabbed the handle and pulled it shut quickly, but he knew Dean had already seen.

“Dean what the hell!” Sam's heart was pounding in his ears.

Dean's voice came softly from the other side of the door. “I uh... I saw you go in there, Sammy... I've been standing out here trying to decide what I should do... if I should...”

“Are you... you're not gonna tell dad are you... I just wanted to see... I mean I thought it would be funny!” Sam tried to turn things around. They could still walk away laughing right? Dean didn't buy it.

“Sam you don't have to lie to me.”

“Really, Dean! It was just a joke. I was gonna show you and we were have a laugh that's all!”

“...so why aren't we laughing?”

“'Cause... 'cause you were peeping on me like a total creep! Why did you open the door?”

“I...” He spoke so quietly Sam almost missed it. “I wanted to see it.”

It was so quiet just so loud for a moment. All Sam could hear was his heart pounding in his rib cage. “What?”

“Sammy... can I?” He sounded so fragile. Like his heart couldn't bare it if Sam told him no. But why in hell would Dean want to see his little brother dressed up like a girl? Like a slutty girl for that matter. It wasn't because... Because Sam told himself that was never going to happen.

Sam let go of the handle and a moment later Dean opened the door again. Sam looked out the door nervously so Dean came inside and closed it before the creepy broom guy could spot them.

Dean's eyes were locked on the blue fabric. Sam bit his lip nervously. He wanted to say something, but he felt frozen.

“So, pretty,” he whispered like he hadn't meant to.

“Dean?” Sam asked so very quietly. Dean looked up at him and wondered if he could see the vulnerability in his eyes. He needed Dean not to hate him for this.

Instead of literally anything Sam was expecting, Dean looked him in the eye and said, “ _You're_ so pretty, Sammy.”

He looked so serious, but he couldn't mean it could he? It had to be a joke. He was mocking him right? Sam didn't know what to say. He didn't know what to do. He just stood there with his hands at his sides, staring at his brother with blushing red cheeks.

Dean shook his head seeming almost frustrated. “You're supposed to be the smart one you know,” he muttered. Sam was only more confused until Dean reached for him. He put one hand on the back of Sam's neck and pulled him in for a kiss.

Sam melted into it with no resistance. No more questions, no more confusion. Somehow this just didn't make sense, but it felt right. Like they were supposed to be like this all along. Not to mention, Dean's tongue in his mouth was probably the greatest thing that had ever happened to anyone ever.

Sam wasn't aware of all the moaning he was doing until he suddenly was and he remembered where they were. He turned his head away from Dean's, without moving his body away as the two of them were now pressed together from chest to hips and there wasn't a force on earth that could make Sam move of his own free will.

“We shouldn't do this here,” he whispered, embarrassed again by his breathlessness.

“Where should we do this? Back at the motel with dad hovering over us. We might not get another chance. Not for a long time... and I've already been waiting so long.”

“Me too.”

Dean groaned and pulled Sam closer so he could press their lips together again. He wrapped his arms around his younger brother and held him tightly and when they paused for breath each exhale sounded like “ _Sammy_ ”. He backed his brother into the wall and pressed kissed down his neck. He moved a hand down to feel where Sam was making a tent in his skirt.

“Can I Sam,” he breathed.

Sam nodded. Dean looked at his bitten lip and his bangs half covering one eye. Why'd he have to be so damn pretty? He reached a hand under Sam's skirt and found the band of his underwear. He shoved them down and Sam helped him kick them off. Then finally, he had his hand wrapped around Sam's cock. It was hot and smooth and Sam whined when he stroked it. More than anything he wanted to watch Sam turn into a wet mess pinned here between him and the wall of the changing room.

Sam's head thumped back against the wall as Dean stroked his cock. His deep kisses muffled the sounds that Sam couldn't hold back. Dean's hand on his dick felt better than anything. Better than his own hand or the pillows he sometimes stuck between his thighs or that one time he'd let Julie touch it when they were the only kids to show up for the chess club meeting and the teacher stepped out to take a phone call.

He could barely keep his legs under him. Thankfully, Dean wrapped his other arm around his waist. Never breaking away from their kiss, still stroking his cock like he was getting paid for it. He knew just where to touch and how. All of it was making Sam's brain feel like mashed potatoes. He could feel his orgasm building up. Sam couldn't help the little sounds he made.

“Dean, I'm gonna cum,” he panted. His brother groaned.

“Do it, Sammy. Cum for your big brother all over your little skirt.”

Sam whined. His long fingers squeezed Dean's arms through the leather of his jacket. His head knocked against the wall again as he almost collapsed. Only Dean stopped him from hitting the floor. He bit his lip to hold in the sounds he wanted to make as he made a mess out of that little blue skirt. Dean held him while he caught his breath.

“Let's get out of here before someone comes to investigate.” He pulled the skirt from around Sam's waist and cleaned him up with it. Sam put his own clothes back on before hurrying out to finish their shopping. He didn't see Dean stuff the little blue scrap of fabric down the back of his jeans, but he'd sure as hell be seeing it again while Dad was gone.

**Author's Note:**

> [Follow my writing blog](http://babybatscreations.tumblr.com)


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